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Longboat Key’s span crosses through both Sarasota and Manatee Counties. Gulf of Mexico Drive is the magnificently landscaped thoroughfare that runs the full length of Longboat Key. It winds past splendid homes and condominiums, lush greenways and parks, hidden driveways and side streets, yacht basins and captivating stretches of the Gulf of Mexico. Along both sides are discreet shopping plazas filled with upscale shopping and fine dining.